CN109485626B - Method for extracting guaiane type sesquiterpene from artichoke - Google Patents
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Abstract
The invention provides a method for extracting guaiane type sesquiterpene from artichoke. The method comprises the steps of crushing artichoke, and leaching with ethanol water solution to obtain a crude extract; loading the crude extract to AB-8 type macroporous resin chromatographic column for eluting, detecting by chromatography, collecting eluate containing target compound, concentrating, and lyophilizing to obtain crude extract; dissolving the crude extract with 50% methanol, loading to RP-C18 chromatographic column for eluting, detecting by chromatography, collecting eluate containing target compound, concentrating, and lyophilizing to obtain pre-isolate; dissolving the pre-separated substance with 30% methanol water solution, performing liquid phase semi-preparation, collecting fraction containing target compound, concentrating, and lyophilizing to obtain target compound. The method provided by the application can effectively separate the target compound from the artichoke, has high extraction purity and simple extraction method, and is beneficial to deep development of the artichoke.
Description
Technical Field
The invention relates to the field of extraction and purification, and particularly relates to a method for extracting guaiane type sesquiterpene from artichoke.
Background
Artichoke is perennial herb of genus Cynara of family Compositae, also called Cynara scolymus, artichoke, Jerusalem artichoke, Lilium brownii, France lily, its scientific name is Cynara scolymus L. Native to the coast of the Mediterranean sea, south Europe and North Africa, transferred from France to Shanghai China in the 19 th century, and now mainly distributed in Shanghai, Zhejiang, Yunnan, Hunan, Shandong and Beijing. Artichoke has high edible value and is reputed as "vegetable emperor".
The artichoke leaf extract has the effects of resisting oxidation, inhibiting bacteria, resisting cancers and tumors, protecting the liver, reducing blood sugar, improving digestion, improving hypercholesterolemia and the like, and the guaiane hemiditerpenoid lactone serving as a main effective component is expected to be developed into a novel medicament for treating inflammatory diseases (such as rheumatoid arthritis), specific hepatitis B virus and II type diabetes related PTP-1B inhibitors, angiogenesis inhibitors, various cancers and a novel medicament for promoting gastric motility and treating gastric ulcer.
However, the prior art has limited research on the separation and purification of the active ingredients. How to extract bioactive components such as guaiane type sesquiterpene compounds from artichoke is extremely important for deeply developing artichoke crops.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
The invention aims to provide a method for extracting guaiane type sesquiterpene from artichoke, which is used for extracting a target compound from the artichoke and has the advantages of rapidness, effectiveness and high purity.
In order to achieve the above purpose of the present invention, the following technical solutions are adopted:
a method for the extraction of guaiane-type sesquiterpenes from artichoke, comprising the steps of:
A. pulverizing globe artichoke, and extracting with ethanol water solution to obtain crude extractive solution;
B. loading the crude extract to an AB-8 type macroporous resin chromatographic column, sequentially eluting with water and ethanol aqueous solutions with volume fractions of 20%, 50% and 80%, detecting by chromatography, collecting eluate containing a target compound, concentrating, and lyophilizing to obtain a crude extract;
C. dissolving the crude extract by using a methanol aqueous solution with the volume fraction of 50%, loading the dissolved crude extract to an RP-C18 chromatographic column, sequentially eluting by using methanol aqueous solutions with the volume fractions of 30%, 48% and 100%, carrying out chromatographic detection, collecting eluent containing the target compound, concentrating and freeze-drying to obtain a pre-isolate;
D. dissolving the pre-separated substance by using a methanol aqueous solution with the volume fraction of 30%, performing liquid-phase semi-preparation by using a Venusil MP C18 chromatographic column and using a mobile phase A as methanol and a mobile phase B as a formic acid aqueous solution as mobile phases, collecting fraction segments containing a target compound, concentrating and freeze-drying to obtain the target compound, wherein the structural formula of the target compound is as follows:
the target compound is effectively separated from the artichoke by using a leaching-AB-8 type macroporous resin column chromatography-RP-C18 column chromatography-methanol/formic acid aqueous solution liquid phase semi-preparation method.
Preferably, the manufacturing method of the AB-8 type macroporous resin chromatographic column comprises the following steps: firstly, soaking AB-8 type macroporous resin particles in absolute ethyl alcohol for 20-24h for pretreatment, then filling the pretreated particles into a column, and washing the column with water until no alcohol smell exists.
The pretreatment is to effectively ensure the separation effect of macroporous resin column chromatography and avoid the interference of impurities.
Preferably, the preparation method of the RP-C18 chromatographic column comprises the following steps: putting RP-C18 particles into methanol for ultrasonic treatment, and continuously stirring to remove bubbles; the treated particles of RP-C18 were then packed in a column with methanol.
More preferably, the specification of the RP-C18 particles is: the thickness of the film is 40-60 mu m,
the C18 chromatographic column packing and preparation method are also selected to maximize the effective separation of the target compound from the complex components. The filler is treated by methanol ultrasonic wave, so that impurities in the filler can be effectively removed, bubbles can be removed, and the effect of column chromatography can be ensured.
Preferably, the Venusil MP C18 chromatographic column has the specifications: 10mm X250 mm, 5 μm.
Further preferably, the volume fraction of the aqueous formic acid solution in the mobile phase B is 0.1%.
More preferably, the liquid phase semi-preparative elution gradient is: initially-30 minutes, the volume ratio of mobile phase a to mobile phase B is 30: 70; 31 minutes to 40 minutes, and the volume ratio of the mobile phase A to the mobile phase B is 100: 0.
The target compound in the complex components can be further separated quickly and efficiently by a proper chromatographic column, a proper mobile phase and an appropriate elution gradient, so that the separation becomes efficient and controllable.
Preferably, in the step a: the material-liquid ratio of the artichoke to the ethanol water solution is 1: 8-10.
Further preferably, the leaching time is 70-72 h.
Optionally, the volume fraction of the aqueous ethanol solution is 70%.
The optimization of the leaching method is to improve the extraction yield on one hand, ensure certain selectivity on the other hand, and cannot damage the structure of a target compound.
Compared with the prior art, the invention has the beneficial effects that:
(1) isolating the target compound from artichoke;
(2) the extraction method provided by the application is simple and effective, and is suitable for popularization and application.
(3) The extraction purity of the target compound is high.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below.
FIG. 1 is a spectrum of a liquid phase semi-preparation carried out in example 1;
FIG. 2 is a graph showing the purity measurement of the objective compound prepared in example 1;
FIG. 3 is a mass spectrum of a target compound prepared according to the present application;
FIG. 4 is a chart of the target compound prepared in the present application as H;
FIG. 5 is a C spectrum of a target compound prepared according to the present application;
FIG. 6 is a chart of the H-H COSY of the target compound prepared in the present application;
FIG. 7 is an HSQC spectrum of a target compound prepared according to the present application;
fig. 8 is a HMBC spectrum of a target compound prepared in the present application.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1
Sun-drying globe artichoke, pulverizing with a pulverizer, adding globe artichoke powder into 70% ethanol water solution at a material-to-liquid ratio of 1:10 at room temperature, extracting for 72 hr while stirring, vacuum filtering with filter cloth, vacuum filtering with filter paper, and concentrating the filtrate under reduced pressure to obtain crude extract. The solid content of the crude extract was 0.1 g/mL.
Soaking AB-8 type macroporous resin in anhydrous ethanol for 24 hr while stirring. Then, the resin particles and absolute ethyl alcohol are loaded into a column (the volume of the column is 1L), and the column is washed by the absolute ethyl alcohol until the effluent is not turbid by adding water (1: 5), and then washed by pure water until no alcohol smell exists. When pure water in the column is placed to be in phase with the resin, 1L of crude extract is slowly added into the chromatographic column, effluent liquid (light green and brown yellow) with obvious color is received after the resin at the lower layer of the column is completely dyed with color, and liquid inlet phase analysis is carried out to avoid the phenomena of excessive samples, incomplete adsorption of macroporous resin and overload. After the sample is completely adsorbed, eluting with water, 20% by volume of ethanol aqueous solution, 50% by volume of ethanol aqueous solution and 80% by volume of ethanol aqueous solution in sequence until the sample is colorless (unchanged), and simultaneously collecting fractions (one fraction per 400 mL) by using a clean glass bottle. The fractions thus obtained were designated as A1, A2 and A3 … …. The collected fractions were filtered through a 0.45 μm filter and then subjected to high performance liquid chromatography. Liquid chromatography detection conditions: the type of the chromatographic column is Venusil MP C18, 4.6mm multiplied by 250mm, 5 μm; the detection wavelength was 205nm, the mobile phase A was methanol, the mobile phase B was 0.1% formic acid water, and the sample size was 20. mu.L. The elution gradient was: initially, the volume ratio of mobile phase a to mobile phase B was 5: 95; to 100% methanol over 30 minutes. Combining according to the detection result, selecting active component A27-29 for further separation and purification, concentrating and freeze-drying to obtain crude extract.
A filler of RP-C18 (60 μm,
) Putting into methanol for ultrasonic treatment, and continuously stirring in the ultrasonic process to remove bubbles. The treated RP-C18 packing was then packed in a column (column volume 1.2L) together with methanol. The crude extract was dissolved with 50% volume fraction aqueous methanol and then slowly loaded. Elution was performed sequentially with 30% methanol, 48% methanol and 100% methanol by volume fraction. And (3) receiving eluent while eluting, wherein each 400mL fraction is sequentially numbered as follows: c1, C2 and C3 … …. And (4) combining according to HPLC detection results, taking C5-10, combining, concentrating under reduced pressure, and freeze-drying to obtain a pre-isolate.
The pre-isolate was dissolved in 30% volume fraction aqueous methanol, and using LC3000 high performance liquid chromatography, Venusil MP C18 column (10mm × 250mm, 5 μm), mobile phase a as methanol, mobile phase B as 0.1% volume fraction aqueous formic acid as mobile phase, the elution gradient was: initially-30 minutes, the volume ratio of mobile phase a to mobile phase B is 30: 70; 31 minutes to 40 minutes, and the volume ratio of the mobile phase A to the mobile phase B is 100: 0. Controlling the sample amount to be 80 μ L, the flow rate to be 3mL/min and the detection wavelength to be 205nm, performing liquid-phase semi-preparation, collecting the fraction containing the target compound (see the peak of No. 12 in figure 1), concentrating and freeze-drying to obtain the target compound.
Purity determination of the target compound: methanol-formic acid aqueous solution (methanol to formic acid aqueous solution volume ratio of 30:70, formic acid aqueous solution volume fraction of 0.1%) was used as a mobile phase, and the mobile phase was purified by LC3000 high performance liquid chromatography, Venusil MP C18(4.6mm × 250mm, 5 μm), detector: UV205nm, flow rate controlled at 1 mL/min. The purity was found to be 96.1% (see FIG. 2) and the extraction yield was 109.1 mg/kg.
Example 2
Sun-drying globe artichoke, pulverizing with a pulverizer, adding globe artichoke powder into 70% ethanol water solution at a ratio of 1:8 at room temperature, extracting for 70 hr while stirring, vacuum filtering with filter cloth, vacuum filtering with filter paper, and concentrating the filtrate under reduced pressure to obtain crude extract.
Soaking AB-8 type macroporous resin in anhydrous ethanol for 20 hr while stirring. Then, the resin particles and absolute ethyl alcohol are loaded into a column (the volume of the column is 1L) together, and the column is washed by the absolute ethyl alcohol until the effluent liquid is added with water (1: 5) and is not turbid, and then the column is washed by pure water until no alcohol smell exists. When pure water in the column is placed to be in phase with the resin, 1L of crude extract is slowly added into the chromatographic column, effluent liquid (light green and brown yellow) with obvious color is received after the resin at the lower layer of the column is completely dyed with color, and liquid inlet phase analysis is carried out to avoid the phenomena of excessive samples, incomplete adsorption of macroporous resin and overload. After the sample is completely adsorbed, eluting with water, 20% by volume of ethanol aqueous solution, 50% by volume of ethanol aqueous solution and 80% by volume of ethanol aqueous solution in sequence until the sample is colorless (unchanged), and simultaneously collecting fractions (one fraction per 400 mL) by using a clean glass bottle. The fractions thus obtained were designated as A1, A2 and A3 … …. The collected fractions were filtered through a 0.45 μm filter and subjected to high performance liquid chromatography. Liquid chromatography detection conditions: the type of the chromatographic column is Venusil MP C18, 4.6mm multiplied by 250mm, 5 μm; the detection wavelength was 205nm, the mobile phase A was methanol, the mobile phase B was 0.1% formic acid water, and the sample size was 20. mu.L. The elution gradient was: initially, the volume ratio of mobile phase a to mobile phase B was 5: 95; to 100% methanol over 30 minutes. Combining according to the detection result, selecting active component A27-29 for further separation and purification, concentrating and freeze-drying to obtain crude extract.
A filler of RP-C18 (40 μm,
) Putting into methanol for ultrasonic treatment, and continuously stirring in the ultrasonic process to remove bubbles. The treated RP-C18 packing was then packed in a column (column volume 1.2L) together with methanol. The crude extract was dissolved with 50% volume fraction aqueous methanol and then slowly loaded. Elution was performed sequentially with 30% methanol, 48% methanol and 100% methanol by volume fraction. Eluting while receiving the eluent, each time400mL of the following fractions are numbered in sequence: c1, C2, C3 … …. And (4) combining according to HPLC detection results, taking C5-10, combining, concentrating under reduced pressure, and freeze-drying to obtain a pre-isolate.
The pre-isolate was dissolved in 30% volume fraction aqueous methanol, and using LC3000 high performance liquid chromatography, Venusil MP C18 column (10mm × 250mm, 5 μm), mobile phase a as methanol, mobile phase B as 0.1% volume fraction aqueous formic acid as mobile phase, the elution gradient was: initially-30 minutes, the volume ratio of mobile phase a to mobile phase B is 30: 70; 31 minutes to 40 minutes, and the volume ratio of the mobile phase A to the mobile phase B is 100: 0. Controlling the sample amount to be 80 mu L, the flow rate to be 3mL/min and the detection wavelength to be 205nm, carrying out liquid phase semi-preparation, collecting fractions containing the target compound, and carrying out concentration and freeze-drying to obtain the target compound.
Example 3
Sun-drying globe artichoke, pulverizing with a pulverizer, adding globe artichoke powder into 70% ethanol water solution at a ratio of 1:9 at room temperature, extracting for 71 hr while stirring, vacuum filtering with filter cloth, vacuum filtering with filter paper, and concentrating the filtrate under reduced pressure to obtain crude extract.
Soaking AB-8 type macroporous resin in anhydrous ethanol for 22 hr under stirring. Then, the resin particles and absolute ethyl alcohol are loaded into a column (the volume of the column is 1L), and the column is washed by the absolute ethyl alcohol until the effluent is not turbid by adding water (1: 5), and then washed by pure water until no alcohol smell exists. When pure water in the column is placed to be in phase with the resin, 1L of crude extract is slowly added into the chromatographic column, effluent liquid (light green and brown yellow) with obvious color is received after the resin at the lower layer of the column is completely dyed with color, and liquid inlet phase analysis is carried out to avoid the phenomena of excessive samples, incomplete adsorption of macroporous resin and overload. After the sample is completely adsorbed, eluting with water, 20% by volume of ethanol aqueous solution, 50% by volume of ethanol aqueous solution and 80% by volume of ethanol aqueous solution in sequence until the sample is colorless (constant), and simultaneously collecting fractions (one fraction per 400 mL) by using a clean glass bottle. The fractions obtained were designated as A1, A2 and A3 … …. The collected fractions were filtered through a 0.45 μm filter and then subjected to high performance liquid chromatography. Liquid chromatography detection conditions: the type of the chromatographic column is Venusil MP C18, 4.6mm multiplied by 250mm, 5 μm; the detection wavelength was 205nm, the mobile phase A was methanol, the mobile phase B was 0.1% formic acid water, and the sample size was 20. mu.L. The elution gradient was: initially, the volume ratio of mobile phase a to mobile phase B was 5: 95; to 100% methanol over 30 minutes. Combining according to the detection result, selecting active component A27-29 for further separation and purification, concentrating and freeze-drying to obtain crude extract.
A filler of RP-C18 (50 μm,
) Putting into methanol for ultrasonic treatment, and continuously stirring in the ultrasonic process to remove bubbles. The treated RP-C18 packing was then packed in a column (column volume 1.2L) together with methanol. The crude extract was dissolved with 50% volume fraction aqueous methanol and then slowly loaded. Elution was performed sequentially with 30% methanol, 48% methanol and 100% methanol by volume fraction. And (3) receiving eluent while eluting, wherein each 400mL fraction is sequentially numbered as follows: c1, C2 and C3 … …. And (4) combining according to HPLC detection results, taking C5-10, combining, concentrating under reduced pressure, and freeze-drying to obtain a pre-isolate.
The pre-isolate was dissolved in 30% volume fraction aqueous methanol, and using LC3000 high performance liquid chromatography, Venusil MP C18 column (10mm × 250mm, 5 μm), mobile phase a as methanol, mobile phase B as 0.1% volume fraction aqueous formic acid as mobile phase, the elution gradient was: initially-30 minutes, the volume ratio of mobile phase a to mobile phase B is 30: 70; 31 minutes to 40 minutes, and the volume ratio of the mobile phase A to the mobile phase B is 100: 0. Controlling the sample amount to be 80 mu L, the flow rate to be 3mL/min and the detection wavelength to be 205nm, carrying out liquid phase semi-preparation, collecting fractions containing the target compound, and carrying out concentration and freeze-drying to obtain the target compound.
The compound monomers obtained in examples 1 to 3 were subjected to LC-MS measurement and NMR detection.
As shown in FIG. 3, M/z339.0928[ M + Na ]] + It is presumed that it has a formula of C 15 H 21 ClO 5 。
Peaks were assigned for the H spectrum (see fig. 4) and the C spectrum (see fig. 5):
1 in H-NMR, the peak at delta 4.90 is the water peak; delta 5.01 is a group of single peaks which are known to contain two protons through integral area, and therefore, the proton signal of the olefin is deduced; δ 1.20 is a set of methyl signals; the signal of the high field part should be a plurality of sets-CH 2 -radical proton signal. 13 In C-NMR, a peak around. delta.48 was a solvent peak (deuterated methanol). The solvent peak was removed and the spectra had a total of 15 carbon signals, which was consistent with the mass spectra findings.
Peaks of the H and C spectra were assigned as follows:
1 H-NMR:2.82(1H,f,J＝6.0Hz,H-1),2.03(1H,m,H-2a),1.69(1H,f,J＝11.0Hz,H-2b),3.63(1H,dt,J＝10.0Hz,5.0Hz,H-3),1.77(1H,m,H-4),1.96(1H,f,J＝9.0Hz,H-5),4.15(1H,t,J＝10.0Hz,H-6),2.39(1H,t,J＝10.0Hz,H-7),3.97(1H,dt,J＝10.0Hz,4.0Hz,H-8),2.77(1H,dd,J＝12.0Hz,4.0Hz,H-9a),2.08(1H,t,J＝11.0Hz,H-9b),4.08(1H,d,J＝11.0Hz,H-13a),3.72(1H,d,J＝11.0Hz,H-13b),5.01(2H,s,H-14),1.20(3H,d,J＝6.0Hz,H-15)。
13 C-NMR:41.61(C-1),37.66(C-2),77.14(C-3),46.41(C-4),51.29(C-5),81.03(C-6),60.18(C-7),69.64(C-8),46.59(C-9),143.81(C-10),77.53(C-11),176.66(C-12),42.49(C-13),113.56(C-14),17.41(C-15)。
the H-H COSY (shown in figure 6) spectrum of the compound is quite clear, and other signals have coupling split conditions except that delta 5.01 is a group of single peaks, so that great help is brought to the analysis. In HSQC (see fig. 7), δ 42.49 corresponds to δ 4.08(H, d, J ═ 10.0Hz) and 3.72(H, d, J ═ 11.0Hz), respectively; δ 46.59 corresponds to δ 2.77(H, dd, J ═ 12.0Hz/4.0Hz) and 2.08(H, d, J ═ 11.0Hz), respectively; δ 37.66 corresponds to δ 2.03(H, m) and 1.69(H, f, J ═ 11.0Hz), respectively, indicating that the three signals are-CH 2-groups. The connection sites of different fragments can be determined by HMBC (shown in figure 8) in combination with H-H COSY and HSQC, and the compound is identified as Cynarinin B (one of guaiane sesquiterpene lactones) by integrating all nuclear magnetic spectrograms and mass spectrometry results. The target compound has the structural formula:
the method for extracting the guaiane type sesquiterpene from the artichoke separates and extracts the target compound from the artichoke, is simple and practical, is suitable for large-scale application, has high product purity, and has positive significance for deep development and utilization of the artichoke.
While particular embodiments of the present invention have been illustrated and described, it would be obvious that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.
Claims (7)
1. A process for the extraction of guaiane-type sesquiterpenes from artichoke, comprising the steps of:
A. pulverizing globe artichoke, and extracting with ethanol water solution to obtain crude extractive solution;
B. loading the crude extract to an AB-8 type macroporous resin chromatographic column, sequentially performing gradient elution by using water and ethanol aqueous solutions with volume fractions of 20%, 50% and 80%, performing chromatographic detection, collecting eluent containing a target compound, concentrating and freeze-drying to obtain a crude extract;
C. dissolving the crude extract by using a methanol aqueous solution with the volume fraction of 50%, loading the dissolved crude extract to an RP-C18 chromatographic column, sequentially carrying out gradient elution by using methanol aqueous solutions with the volume fractions of 30%, 48% and 100%, carrying out chromatographic detection, collecting eluent containing the target compound, concentrating and freeze-drying to obtain a pre-isolate;
D. dissolving the pre-separated substance by using a methanol aqueous solution with the volume fraction of 30%, performing liquid-phase semi-preparation by using a Venusil MP C18 chromatographic column and using a mobile phase A as methanol and a mobile phase B as a formic acid aqueous solution as mobile phases, collecting fraction sections containing a target compound, concentrating and freeze-drying to obtain the target compound; the specifications of the VenusilMP C18 chromatographic column are as follows: 10mm × 250mm, 5 μm; the volume fraction of the formic acid aqueous solution in the mobile phase B is 0.1%; the liquid phase semi-preparative elution gradient was: initially-30 minutes, the volume ratio of mobile phase a to mobile phase B is 30: 70; 31 minutes to 40 minutes, wherein the volume ratio of the mobile phase A to the mobile phase B is 100: 0;
the target compound has a structural formula:
2. the method of claim 1, wherein the AB-8 type macroporous resin chromatographic column is prepared by the following steps: firstly, soaking AB-8 type macroporous resin particles in absolute ethyl alcohol for 20-24h for pretreatment, then filling the pretreated particles into a column, and washing the column with water until no alcohol smell exists.
3. The method of claim 1, wherein the RP-C18 chromatography column is prepared by: putting RP-C18 particles into methanol for ultrasonic treatment, and continuously stirring to remove bubbles; the treated particles of RP-C18 were then packed in a column with methanol.
4. The method of claim 3, wherein the RP-C18 particles are of the specification: the thickness of the film is 40-60 mu m,
5. the method according to claim 1, wherein in step a: the material-liquid ratio of the artichoke to the ethanol water solution is 1: 8-10.
6. A process according to claim 5, wherein the leaching time is 70-72 h.
7. The process according to any one of claims 1 to 6, wherein the volume fraction of the aqueous ethanol solution is 70%.
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| CN105315147A (en) * | 2014-08-03 | 2016-02-10 | 江苏康缘药业股份有限公司 | Guaiane-type sesquiterpenoids compound, and preparation method and application thereof |
| CN108440472A (en) * | 2018-06-11 | 2018-08-24 | 延边大学 | The extraction separation method of sesquiterpene lactone constituents and protection liver and the drug for preventing Fatty Liver Disease in a kind of Artemisia capillaris |
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| CN105315147A (en) * | 2014-08-03 | 2016-02-10 | 江苏康缘药业股份有限公司 | Guaiane-type sesquiterpenoids compound, and preparation method and application thereof |
| CN108440472A (en) * | 2018-06-11 | 2018-08-24 | 延边大学 | The extraction separation method of sesquiterpene lactone constituents and protection liver and the drug for preventing Fatty Liver Disease in a kind of Artemisia capillaris |
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| Sesquiterpenoids from Cynara scolymus;Xiaoli Li et al.;《Heterocycles》;20041203;第65卷(第2期);第287-291页 * |
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